Hi ladies. It's looking like I'll have an opportunity to cross off a bucket list item in a week or so. As many of you know, I'm closeted, and so I only dress when I travel. Coming up in about ten days, I'm going to be hitting a couple different cities in the same week, and in doing so, I'll have a chance to fly pretty between the two. Both flights will be relatively short, though I'll have a layover in O'Hare airport. I'm excited (I know because my heart skips a beat when I think about it), and so I think I'm actually going to do it!

I'm probably going to go in "business woman" travel mode, in that since I'll be travelling on business, it feels appropriate. With that in mind, I'll likely wear a blouse, black skirt, hose, and moderate heels. I'll change somewhere en route to the airport or at the airport, which will require going through security en femme.

With this backdrop in mind, a few questions for all of you.

  1. For those who've flown en femme, what general advice or recommendations would you give based on your experiences?
  2. I'd like to check my bags, partly so I don't have to keep up with them, especially given the layover, and partly so there's no going back! Good or bad idea?
  3. Since I'll have a laptop, I'll need to carry that with me. I usually carry my laptop in my nice leather (Frye) messenger bag. How much will that mess up my identity? I could always try to fit it in my roller bag and carry that with me, but I don't love that idea. Thoughts?
  4. What do I need to have in my purse (besides ID, etc.) just in case?

Thanks in advance for your thoughts! I'm excited!

Steph